Acetic Acid → HCID 19029014, compound

HRID 2256344Notes

Reaction equation

HRID 2256344 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH2:18][CH2:19][CH2:20][N:21]3[CH2:26][CH2:25][N:24]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[CH2:23][CH2:22]3)[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH2:11][NH:10][CH2:9]2)=[CH:4][CH:3]=1.C=O.[C:35]([BH3-])#N.[Na+].C(O)(=O)C>C(#N)C>[ClH:1].[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH2:18][CH2:19][CH2:20][N:21]3[CH2:22][CH2:23][N:24]([C:27]4[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=4)[CH2:25][CH2:26]3)[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH2:11][N:10]([CH3:35])[CH2:9]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 19028848HCID 19028848, compound

Product 1

HCID 19029014HCID 19029014, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 4-(p-chlorophenyl)-4-[3-(4-phenylpiperazin-1-yl)propyl]-1,2,3,4-tetrahydroisoquinoline (0.7 g) in acetonitrile (15 ml) was added formalin (0.64 ml). Then, sodium cyanoborohydride (0.16 g) was added portionwise with stirring. The mixture was stirred for 15 minutes, at the end of which time acetic acid was added dropwise until the solution became neutral. The mixture was further stirred for 2 hours and the reaction mixture was extracted with ethyl acetate-1N aqueous sodium hydroxide solution. The organic layer was washed with water, dried over anhydrous sodium sulfate and concentrated to dryness. The residue was purified by silica gel column chromatography and treated with hydrochloric acid to provde the title compound (0.6 g) as colorless powder.

Workup

  1. additionwas added dropwise until the solution
  2. stirringThe mixture was further stirred for 2 hours
  3. extractionthe reaction mixture was extracted with ethyl acetate-1N aqueous sodium hydroxide solution
  4. washThe organic layer was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated to dryness
  7. customThe residue was purified by silica gel column chromatography
  8. additiontreated with hydrochloric acid

Sources & evidence

ORD record
ord-789f265b4a9345858996486441f0665c
Source dataset
uspto-grants-1997_08
Patent number
US05654296

Reaction notes

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